I’m writing this article as this is my hometown, but there are plenty of other great cities in the Shenandoah Valley and Frederick County area which I serve and think would make a great home for you and yours.

1. Cost of Living

Winchester is one of the most affordable places in the country to move to for retirees. I’m not the only one to notice that! AARP ranked Winchester on their list here: most affordable communities for retirees. Even if you aren’t a retiree, this is still great news! Virginia doesn’t tax Social Security benefits, and it has no estate tax or inheritance tax. Seniors age 65 and older who meet income limits can deduct up to $12,000 each from state income taxes.


The median home price in Frederick is $288,900 currently in 2019, whereas the median price in Fairfax County is $547,400. We can’t forget about property taxes either: Winchester city limits property taxes and surrounding Frederick County are consistently lower than in Manassass and many other cities in Virginia.

Considering the data above, it’s easy to see why more and more people are choosing to retire in Winchester.

2. Restaurants and Food

In the past 15 years alone, the restaurant scene in Winchester has really taken off! We’ve seen the opening of everything from Indian cuisine to Thai. Our foodies in town are plenty busy reviewing away on Yelp and Google, and many are travelling here from all over the region to enjoy some highly rated eateries and digs. Winchester Food Tour is a good resource to check out the sheer number of options we are lucky to have

Winchester also features the old town farmers market. The seasonal market is open throughout the spring and summer seasons. It is a great place to find fresh local food and farm products directly from area farmers. At the same time, it offers a great atmosphere for you to enjoy the surroundings in historic Old Town Winchester. Many vendors attend regularly and it is a great community event for you to meet new people and load up on amazing food.

3. Day Trips

One of the big draws of Winchester is the surrounding small towns with historic landmarks and natural wonders. Washington DC for example is just a short 75 miles away, and it features world-class museums, restaurants, and national heritage. That’s just one example of the many options. Even closer is Luray caverns, the majestic Blue Ridge mountains, Skyline Drive, Shenandoah National Park, and much, much more. Outdoor lovers will find plenty of acclaimed hiking trails and camping locations. Throughout the area can be found farm lands, orchards, vineyards, and beautiful mountain landscapes. Or, if you’re not keen on travelling far, the downtown walking mall is in the middle of Winchester’s historic Old Town district. It features beautiful scenery, dining, craft breweries and beers, historic museums and architecture, and shopping options.

4. Rich History

Winchester has an extremely rich history. This town was founded in 1744 and surveyed by the First President, George Washington. It was a major battlegrounds during the Civil War, and contains well over a dozen official historical locations such as the Patsy Cline House and Fort Loudoun.

Due to its strategic location, Winchester was a prominent location where six Civil War battles took place.

5. Apple Blossom Festival

Annually, Winchester hosts this festival and it is quite a transformation when it occurs. The city has been known as “Apple Capital” due to it being surrounded by apple orchards. People from all over come to Winchester to enjoy the week long Apple Blossom Festival consisting of numerous events. Some of the festivals highlights include a carnival, parades, musical events, lunches, contests, craft showers, fireworks, and much more.

6. Schools

Winchester City public schools are highly rated in the state. The student-teacher ratio is consistently one of the lowest available. There are four different high schools and a large number of elementary and middle schools. Students in Winchester are afforded great opportunities for sports and academics.

Additionally, Winchester is home to two colleges: Shenandoah University and Lord Fairfax Community College. SU is a private, nationally recognized institution with 49 undergraduate degree programs and 26 graduate programs. According to their website, is had 3,817 students in the Fall 2018 semester. It sits on a beautiful resident campus and has a great life for students providing performing arts, athletics, and other events almost daily.

7. Entertainment

Whether you’re interested in catching a live band, theatre performance, or going out with some friends for a meal and drink, Winchester has a little something for everybody! Check out some of the local entertainment options:

-Alamo Drafthouse Cinema: Modern movie theater with a full menu. They will bring your food straight to your movie seating!

-Blue Fox Billiards: A great place to hang out on weekdays and weekends if you like live music. Offers multiple billiards tables, live music acts travelling from the region, and a great place to enjoy some American cuisine.

-Bright Box Theater- Venue located on the Old Town Walking Mall that showcases a wide variety of different acts: comedy, live music. and other entertainment.

-Bars and Pubs- Where do we begin? 50/50 Taphouse, 147 North, Union Jack, Piccadilly’s, Brewbaker’s, Escutcheon Brewing Co., Cork Street Tavern, IJ Canns, James Charles Winery, Milano’s, Nana’s Irish Pub, Sweet Nola’s, and much much more

8. Scenic Living

A short drive through the area will make quickly make you realize why the region is such a popular tourist destination. The Northern Shwenandoah Valley is located in NW Virginia, with Maryland to the north and West Virginia to the west side. Large swathes of forests, national parks, waterways, caves, and historical sites are abundant. Experience the four seasons with the amazing climate and weather that is fairly unique to this corner of the world.

Picturesque, postcard-worth farms are spread throughout the peaceful country roads. There are many natural wonders, such as the Luray caverns nearby. Renowned hiking trails for all levels of adventurer are found throughout the area. Horseback riding, water tubing, and numerous other outdoor activities are available for those who love to embrace the great outdoors.

9. Top-notch Medical Access

Winchester Medical Center is a a medical facility supporting the top of Virginia an West Virginia. With world class facilities, they offer many different specialties and services. Valley Health, a part of WMC, has an excellent wellness and fitness center that offers exercise programs, classes, personal training, and weight maintenance programs side-by-side with physical therapy programs.

10. Industry

The area has a large up-and-coming industry along with major, established industries. The main industries are education, health and social services, manufacturing, and food processing. The major employment sectors in Winchester are educational services, construction, healthcare, food services, management and professional services, and plastic and rubber products. Winchester has been making headlines as one of the best places for small businesses to begin. It also has a large number of employment options. Some of the larger employers in the area include Amazon, McKeeson, Rubbermaid, and Valley Health.